Optical rotations were obtained using a Perkin–Elmer 241 automatic polarimeter (Perkin Elmer, Waltham, MA, USA), Absorption spectra were recorded by an ultraviolet-visible (UV-vis) light spectrophotometer (Lambda 35, PerkinElmer, Norwalk, CT, USA), Electronic Circular dichroism (CD) spectra were recorded on a Brighttime Chirascan spectrometer (Applied Photophysics Ltd., Leatherhead, UK); FTIR spectra were obtained by using a FTIR spectrometer (PerkinElmer, Norwalk, CT, USA); NMR spectra were taken on a Bruker AVANCE III 500 spectrometer (Bruker, Bremen, Germany); HRESIMS data were carried out on an Agilent 6210 ESI-TOF mass spectrometer (Agilent, Santa Clara, CA, USA); Silica gel (Qingdao Haiyang Chemical Group Co., Qingdao, China) and Sephadex LH-20 (Amersham Biosciences, Chicago, IL, USA) were used for column chromatography, Waters 1525 semi-preparative HPLC (Waters, MA, USA) coupled with a Waters 2996 photodiode array detector. A Kromasil C18 preparative HPLC column (250 mm × 10 mm, 5 μm) was used. Thin layer chromatographies (TLCs) (Merck, Darmstadt, Germany) were performed on silica-gel F254 plates and visualized under UV light, and by heating after spraying with 10% aq. H2SO4.
Agilent 6210 esi tof mass spectrometer
Manufactured by Agilent Technologies
Sourced in United States
The Agilent 6210 ESI/TOF mass spectrometer is a high-performance instrument designed for accurate mass measurements. It utilizes electrospray ionization (ESI) and time-of-flight (TOF) mass analysis to provide precise and reliable data for a wide range of applications.
Automatically generated - may contain errors
Lab products found in correlation
Sephadex lh 20, by Cytiva (2 mentions)
Sephadex lh 20, by GE Healthcare (2 mentions)
Ftir spectrometer, by PerkinElmer (1 mentions)
Waters 2996 photodiode array detector, by Waters Corporation (1 mentions)
Lambda 35, by PerkinElmer (1 mentions)
Avance 3 500 spectrometer, by Bruker (1 mentions)
Quartz cuvette, by Hellma (1 mentions)
Drx 400, by Bruker (1 mentions)
Avance spectrometer, by Bruker (1 mentions)
Szx16 fluorescence microscope, by Olympus (1 mentions)
Dp2 bsw image acquisition system, by Olympus (1 mentions)
Epoch microplate spectrophotometer, by Agilent Technologies (1 mentions)
Transparent 96 well plate, by Greiner (1 mentions)
Luna c18 column, by Phenomenex (1 mentions)
Luna c18 column, by Waters Corporation (1 mentions)
Iproh, by Merck Group (1 mentions)
Drx 400 spectrometer, by Bruker (1 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (1 mentions)
N n dimethylformamide (dmf), by Merck Group (1 mentions)
Avance neo, by Bruker (1 mentions)
11 protocols using agilent 6210 esi tof mass spectrometer
1
Comprehensive Analytical Characterization of Natural Products
2
Characterization of NBD-DMA and NBD-DDA Compounds
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1H and 13C NMR spectra were recorded on an ECP500 (JEOL; NBD-DMA) or an ECP600 (JEOL; NBD-DDA) at a proton resonance frequency of 500 MHz and 600 MHz, respectively, and calibrated to the residual solvent signals at δ 7.26 (1H) and δ 77.16 (13C) for chloroform and δ 2.50 (1H) and δ 39.52 (13C) for DMSO (Fulmer et al., 2010 (link)), respectively. Electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS) measurements were done with an Agilent 6,210 ESI-TOF mass spectrometer (Agilent Technologies). The solvent flow rate was adjusted to 4 μl/min, the spray voltage set to 4 kV, and the drying gas flow rate set to 15 psi (1 bar). All other parameters were adjusted to yield a maximum abundance of the relative [M + H] peak. Fluorescence measurements were done at room temperature using dilute solutions of NBD-DDA in 10 mm x 10 mm quartz cuvettes (Hellma GmbH). Fluorescence emission measurements were performed with a calibrated spectrofluorometer FSP-920 (Edinburgh Photonics), equipped with a Xenon lamp and double monochromators. The fluorescence emission spectra were corrected for the wavelength dependent spectral responsivity of the emission channel (emission correction) and the fluorescence excitation spectra for the wavelength dependent spectral radiant power of the excitation spectra (excitation correction) (Resch-Genger et al., 2005 (link)).
3
NMR and HRESIMS Analysis of Compound
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The 1H- and 13C-NMR spectra were measured on a Bruker DRX-400 (Bruker Biospin AG, Fällanden, Germany, 400 MHz for 1H- and 100 MHz for 13C spectra) spectrometer. Chemical shifts were expressed with reference to TMS as the internal standard, and coupling constants (J) were given in Hz. HRESIMS was recorded on an Agilent 6210 ESI/TOF mass spectrometer (Agilent Technologies Inc., San Diego, CA, USA).
4
Fluorescence and NMR Characterization
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Images were observed and captured with an SZX16 fluorescence microscope, a DP2-BSW image acquisition system (Olympus, Tokyo, Japan), and an AXIO-V16 fluorescence microscope (Zeiss, Oberkochen, Germany). An HPG280-BX Illumination Incubator (Donglian Electronic Technology Development Co., Ltd., Harbin, China) was used for zebrafish culture after drug administration. A zebrafish culture system (ESEN Technology Development Co., Ltd., Beijing, China) was used to cultivate the zebrafish. NMR spectra were recorded on a Bruker Avance spectrometer (Bruker, Billerica, MA, USA) operating at 400 (1H) and 100 (13C) MHz with TMS as an internal standard. ESI-MS data were acquired on an Agilent 6210 ESI/TOF mass spectrometer (Agilent, Santa Clara, CA, USA).
5
Spectroscopic Analysis of Organic Compounds
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High-resolution electrospray ionization mass spectrometry (HR-ESI-MS) data were obtained using an Agilent 6210 ESI/TOF mass spectrometer (Agilent Technologies, Santa Clara, CA, USA). Semi-preparative chromatography was performed on a Waters 1525 pump and a 2996 photodiode detector equipped with a Luna C18 column (5 μm, 250 × 10 mm, Phenomenex, Torrance, CA, USA) and used for analytical high-performance liquid chromatography (HPLC; Waters Corporation, Milford, MA, USA) with a Luna C18 column (5 μm, 250 × 4.6 mm). 1H and 13C-nuclear magnetic resonance (NMR) spectra were recorded on a Bruker spectrometer (Bruker BioSpin GmbH, Rheinstetten, Germany) at 400, 600, and 800 MHz for 1H and 100, 150, and 200 MHz for 13C.
Enzyme assays were performed using an Epoch Microplate spectrophotometer (BioTek Instruments, Inc., Winooski, VT, USA) in transparent 96-well plates (Greiner Bio-One, Kremsmünster, Austria). All other reagents and chemicals were purchased from Sigma-Aldrich (Saint Louis, MO, USA) and different commercial suppliers and were of analytical grade.
Enzyme assays were performed using an Epoch Microplate spectrophotometer (BioTek Instruments, Inc., Winooski, VT, USA) in transparent 96-well plates (Greiner Bio-One, Kremsmünster, Austria). All other reagents and chemicals were purchased from Sigma-Aldrich (Saint Louis, MO, USA) and different commercial suppliers and were of analytical grade.
6
Synthesis and Characterization of α-Nitroketones
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The structures of produced compounds were firmly confirmed by 13C NMR and 1HNMR spectra, and supported by HRMS, and IR data (see the Supplementary Materials ).
1H NMR (400 MHz) and 13C NMR (101 MHz) were recorded at room temperature on DRX-400 spectrometer (Bruker, Saarbrücken, Saarland, Germany) in CDCl3. The chemical shifts are given in parts per million (ppm) on the delta (δ) scale. The solvent peak was used as a reference value, for 1H NMR: CDCl3 δH 7.26; for 13C NMR: CDCl3 δC 77.16 ppm. IR spectra were recorded using an Avatar 360 FT-IR ESP spectrometer (Nicolet, Madison, Wisconsin, USA) at room temperature. HR-ESI-MS spectra were acquired using an Agilent 6210 ESI/TOF mass spectrometer (Agilent Technologies, Santa Clara, CA, USA). Analytical TLC was conducted on silica gel plates (GF254, Yantai Institute of Chemical Technology, Yantai, China). Spots on the plates were observed under UV light. Column chromatography was performed on silica gel (200~300 mesh and 300~400 mesh; Qingdao Marine Chemical Factory, Qingdao, China). Super-dry solvent i-PrOH, ACN, DMSO and DMF were purchased from Aldrich and used as supplied. The α-nitroketones were synthesized using the same method as reported in the literature [48 ,49 ].
1H NMR (400 MHz) and 13C NMR (101 MHz) were recorded at room temperature on DRX-400 spectrometer (Bruker, Saarbrücken, Saarland, Germany) in CDCl3. The chemical shifts are given in parts per million (ppm) on the delta (δ) scale. The solvent peak was used as a reference value, for 1H NMR: CDCl3 δH 7.26; for 13C NMR: CDCl3 δC 77.16 ppm. IR spectra were recorded using an Avatar 360 FT-IR ESP spectrometer (Nicolet, Madison, Wisconsin, USA) at room temperature. HR-ESI-MS spectra were acquired using an Agilent 6210 ESI/TOF mass spectrometer (Agilent Technologies, Santa Clara, CA, USA). Analytical TLC was conducted on silica gel plates (GF254, Yantai Institute of Chemical Technology, Yantai, China). Spots on the plates were observed under UV light. Column chromatography was performed on silica gel (200~300 mesh and 300~400 mesh; Qingdao Marine Chemical Factory, Qingdao, China). Super-dry solvent i-PrOH, ACN, DMSO and DMF were purchased from Aldrich and used as supplied. The α-nitroketones were synthesized using the same method as reported in the literature [48 ,49 ].
7
Spectroscopic Characterization of Compounds
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Nuclear magnetic resonance (NMR) spectroscopy was performed on a Bruker Avance NEO (600 MHz for 1H and 150 MHz for 13C) spectrometer (Bruker, Karlsruhe, Germany). The chemical shifts (δ) are given in ppm and coupling constants (J) are given in hertz (Hz). HRESIMS data were obtained on an Agilent 6210 ESI/TOF mass spectrometer (Agilent, Santa Clara, CA, USA). UV spectra were recorded on an Agilent UV-Vis Cary 60 spectrometer (Agilent Corporation, Santa Clara, CA, USA). IR spectra were recorded on a Nicolet iS5 FT-IR spectrometer. ECD spectra were obtained by an Applied Photophysics Chirascan circular dichroism spectrometer. Optical rotations were recorded on a Horiba SEPA-300 polarimeter. Semi-preparative HPLC was performed on an Agilent 1100 (Agilent Technologies, Santa Clara, CA, USA). The columns were a Waters C18 (5 µm, 10 mm × 250 mm) column (Made in Ireland) and a Hungpu phenyl (5 µm, 10 mm × 250 mm) column (Guangzhou Hungpu Technology Co., Ltd., Guangzhou, China). Silica gel (60–80, 200–300, and 300–400 mesh, Qingdao Marine Chemical Co. Ltd., Qingdao, China) and Sephadex LH-20 (25–100 µm, Amersham Biosciences, Uppsala, Sweden) were used for column chromatography (CC). TLC was conducted on pre-coated silica gel GF254 plates (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China), and spots were detected by spraying with 5% H2SO4 in EtOH followed by heating.
8
Spectroscopic and Chromatographic Techniques
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Optical rotations were measured on a JASCO P-2000 digital polarimeter (JASCO, Tokyo, Japan). UV spectra were performed on an Eppendorf BioSpectrometer Basic photometer. IR spectra were recorded on a JASCO FT/IR-4600 spectrometer in KBr discs. CD data were obtained on a JASCO J-810 spectropolarimeter. NMR spectra were collected using a JEOL JNM-ECP 600 spectrometer (JEOL, Tokyo, Japan). HRESIMS data were acquired on an Agilent 6210 ESI/TOF mass spectrometer (Agilent, Santa Clara, CA, USA). Analytical high performance liquid chromatography (HPLC) system (Waters, Milford, MA, USA) consisted of Waters e2695, UV Detector 2489, and software Empower using a C18 column (Diamonsil C18(2), 250 × 4.6 mm, 5 μM). Semipreparative HPLC was operated on the same system using a C18 column (Cosmosil 5C18-MS-II, 250 × 10 mm, 5 μM). Vacuum-liquid chromatography (VLC) used silica gel H (Qingdao Marine Chemical Factory, Qingdao, China). Thin layer chromatography (TLC) and column chromatography were performed on plates pre-coated with silica gel GF254 (10–40 μm) and Sephadex LH-20 (GE Healthcare Biosciences, Uppsala, Sweden), respectively.
9
Chemical Analysis of Natural Compounds
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UV spectra were measured by a JASCO V-550 UV/VIS spectrophotometer (JASCO, Tokyo, Japan). IR spectra were measured by a JASCO FT/IR-480 plus FT-IR spectrometer with KBr pellets (JASCO, Tokyo, Japan). A JASCO P-1020 polarimeter was used for measuring the optical rotations (JASCO, Tokyo, Japan). HRESIMS data were accomplished using an Agilent 6210 ESI/TOF mass spectrometer (Agilent, Massachusetts, United States). ECD spectra were measured by an Applied Photophysics Chirascan plus CD (Applied Photophysics, United Kingdom). NMR spectra were obtained on a Bruker AV-400 spectrometer with TMS as the internal standard (Bruker, Karlsruhe, Germany), and the chemical shifts (δ) are expressed in ppm and coupling constants (J) in Hz. For column chromatography (CC), silica gel (200–300 mesh, Qingdao Marine Chemical Plant, Qingdao, P. R. China), ODS (50 μm, YMC, Kyoto, Japan), and Sephadex LH-20 (Pharmacia Biotech, Uppsala, Sweden) were used. silica gel GF254 plates (Yantai Chemical Industry Research Institute, Yantai, China) were used for thin-layer chromatography (TLC). HPLC separations were performed using a COSMOSIL C18 preparative column (5 μm, 20 × 250 mm). All chemical reagents were purchased from Shandong Yuwang Chemical Company (Shandong, P. R. China).
10
Metabolomic Analysis of Anoxic Embryos
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A metabolomic analysis was performed on 5 hpf WT embryos exposed to 1 hr of anoxia and age-matched normoxic controls (5 hpf). A total of 400 μl of methanol and 400 μl of water were added as a polar solvent to decant the embryos over ice. After decanting, 400 μl of isopropanol was added as a nonpolar solvent. Samples were rocked at 4 ° C for 20 min and centrifuged at 13,000 g for 5 min. The water-soluble metabolites (top of phase separation) was extracted and stored at - 80 °C. Four biological replicates were obtained and 10 embryos were used per sample. Mass spectra were acquired using a Phenomenox Luna NH2 column connected to an Agilent 1200 HPLC and Agilent 6210 ESI-TOF mass spectrometer in a negative ion mode. Data were analyzed with Agilent software packages (MassHunter, Mass Profiler, Profinder and Mass Profiler Professional) using 1000 ion counts as an arbitrary cutoff. An extracted ion chromatograph (EIC) was then generated for each ion. Ions that did not show clear peaks were discarded from the subsequent analysis. Ions were identified by comparing molar mass against Mzed database (Draper et al., 2009 (link)). The lactate peak (observed: 89.0240, calculated mass for M-H ions is 89.0239) was extracted, and the area was used for comparison.
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